Educator stories: The power of the business mindset
Educator Jade Weatherington shares lessons she’s learned over 4 years on Outschool, including how seeing teaching as a business has led to her success on the platform.
sticky notes with business plan elements

Jade Weatherington, known as Teacher Jade on Outschool, has taught virtually on various platforms for 15 years. She joined Outschool 4 years ago – back when there were only around 100 teachers on the platform. Today, she owns the organization Teacher Jade’s Writing Academy and earns enough income from Outschool to call it her full-time career. We sat down with Jade to chat about how she’s built her teaching business and ask her advice for other educators looking to grow.

What every educator needs to know

“Everyone who has success didn’t start off successful,” says Jade. It takes time to learn new skills, grow a business, and gain a following of dedicated learners.

“Especially in the age of social media, it looks like everyone becomes successful overnight. I’ve been teaching online for 15 years, and it took a very long time to build to the point where I am now.”

Jade says if you feel like you’re failing – just stick with it. “My first month on Outschool, I made $36,” she remembers. If she’d given up then, she would never have made it to where she is now.

We wondered – what was the turning point for Jade? How did she go from $36/month on Outschool to much more than that? Turns out, she knew the exact moment she started heading in a new direction.

Teaching is a business

“The most growth for me came in no longer looking at Outschool as a side job, but instead looking at it as a business.”

Speaking with Jade, it’s obvious that she’s passionate about teaching English and making learning an exciting, fun experience. In addition to her talents as an educator, she attributes her success to a pivotal moment that changed her mindset about her online teaching career.

When she first started teaching on Outschool, Jade saw her classes strictly as “side money.” Even when she didn’t have any other income besides her online classes, she still wasn’t thinking of virtual teaching as a career. At the same time, she was also working on developing homeschool products to make extra cash.

“I ended up joining a business cohort, and my mentor asked, ‘Why are you trying to build up these products when you have a service [on Outschool] that’s going so well?’ It was an aha moment. From there, I started shifting my mindset about Outschool. If I’m getting paid to provide a service, then this is a business that I need to help grow. I can’t just sit back and hope that my business grows. I have to put some ‘people power’ behind it to make it actually work.”

By seeing Outschool as her business – not just her side hustle – Jade began incorporating new habits into her routine. Here are a few of the most important things she did to spark earnings and enrollments early on.

1. Pay attention to your stats

Evaluate what’s working for you as an educator – and what’s not. Keep track of which classes are filling up, what times are popular, and which classes parents are requesting the most. For Jade, she realized that to be successful teaching full-time on Outschool, it wasn’t just about “When do I want to work,” but about designing a schedule that met her customers’ needs. (Check out your own teaching stats on your educator dashboard.)

2. Ask for feedback

Jade credits asking learners and parents for feedback as significantly contributing to her success in the beginning.

“Staying in touch with parents helped a lot. When I was first starting out, at the end of my classes I used to ask, ‘What did you like about the class?’ and ‘What would you change about the class?’. I would never ask ‘What didn’t you like?’. [Parents and learners] often give you better critiques when you ask ‘What would you change about the class?’.”

She consistently asked these questions and refined her classes to combine her passions with what families wanted. So much so, that now she says, “I don’t do it much anymore because I’ve had so much feedback that I feel like I’ve perfected my current courses to be exactly how I want them to be.”

3. Create classes based on requests

Jade’s first class was a 4-week course on writing a 5-paragraph essay (a version of which still exists today). How did she decide what came next?

“I’ve developed most of my classes because of requests made by parents… They helped me create classes that built on what I already had available.”

As she was sifting through parent requests, Jade also noticed that many learners were re-enrolling in the exact same classes – ones that weren’t really designed to be taken twice. She realized she needed to create options for families that immediately wanted to re-enroll in classes taught by her. The solution: She offers multiple follow-up courses to many of her multi-day classes (both live and as Flex classes), as well as some ongoing courses. Ongoing classes are particularly beneficial for learners who don’t want to wait for another multi-day section to begin to keep writing with Teacher Jade.

Becoming an organization

With building her business in mind, Jade set a goal to reach more families and expand her class offerings by adding some more of that “people power” and forming Teacher Jade’s Writing Academy. To make the transition to leading an organization as smooth as possible, she hired educators who already taught individual classes on Outschool. She saved time and energy training teachers by taking this approach, and she knew they would feel confident using the platform.

She also prioritized keeping the same atmosphere in classes across her organization, saying:

“If I already have dedicated families who are taking classes from me, they wouldn’t necessarily want to take a class with someone who’s the complete opposite of me… I knew I wanted everyone to be really dynamic and fun while teaching virtually.”

Jade mentioned that it’s easy to move too fast when starting an organization, so be aware of the time required to manage your new educators and class load if you’re considering it! It’s a good idea to create a game plan for how you’ll manage your time or potentially scale back the number of classes you personally teach when transitioning to an organization.

In the end, Jade says it’s all about consistency and dedication to building a business. Remember: “Just stick with it. Be consistent. It takes time to grow.”

To learn more about Jade, visit her organization profile and take a look at a few of her popular classes! You can also watch our full interview with her here.

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